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Formal Aminocyanation of α,β‐Unsaturated Cyclic Enones for the Efficient Synthesis of α‐Amino Ketones
Author(s) -
Sun Chunrui,
O'Connor Matthew J.,
Lee Daesung,
Wink Donald J.,
Milligan Robert D.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201309435
Subject(s) - cycloaddition , alkylation , chemistry , lithium (medication) , molecule , combinatorial chemistry , ketone , organic chemistry , catalysis , biology , endocrinology
Installation of amino functionality on organic molecules through direct CN bond formation is an important research objective. To achieve this goal, a 1,2‐aminocyanation reaction was developed. The reaction occurs through the formation of pyrazolines by means of a formal dipolar cycloaddition of cyclic α,β‐unsaturated ketones with lithium trimethylsilyldiazomethane followed by novel protonolytic NN bond cleavage under mild conditions. This two‐step process provides a diverse array of structurally complex free and mono‐alkylated α‐amino ketones in excellent yields.